MPs have backed a motion aiming to force the government to publish communications linked to prorogation and documents connected to no-deal Brexit planning.
It was a fifth defeat in five days for Boris Johnson, who lost by 311 votes to 302 - a majority of nine.
It could lead to the government being forced to hand over all international correspondence, which includes emails, WhatsApp and Facebook messages.
However a Downing Street source told ITV News Political Editor Robert Peston that "under no circumstances will Number 10 staff comply with Grieve's demands regardless of any votes in Parliament".
The motion lists key individuals of Prime Minister Boris Johnson's Government, including senior adviser Dominic Cummings and director of legislative affairs Nikki Da Costa.
It also asks for documents prepared for the government since July 23 relating to Operation Yellowhammer, connected to no-deal Brexit planning, to be released.
In theory, documents have to now be produced by 11pm on Wednesday, however it is appears unlikely that will happen.
Following the debate Mr Grieve told ITV News he believes the information will be published because "wiser council will prevail".
He said: "If it chooses not to provide the information it is taking effectively a revolutionary step."
He added: "The government is going to have to make up its mind whether it is a bunch of hoodlums who are just smashing the place up while they try to achieve a particular end, or whether in fact they're respectable group."
The defeat means Mr Johnson's government has maintained a 100% record of losing every House of Commons vote held since he became prime minister.
MPs then discussed Labour leader Jeremy Corbyn's application for an emergency debate on the rule of law and ministers' obligation to uphold it.
The government allowed the emergency motion to pass, meaning it is not strictly a defeat as it was not contested, but the opposition will see it as a symbolic victory.
The debate was called amid concerns over the government's expected response to legislation designed to prevent it from forcing through a no-deal Brexit on October 31.
Opening the debate, Mr Corbyn praised the cross-party efforts of MPs, adding: "It is clear there is no mandate for no deal."
He said: "The fact that Parliament is compelled to pass a law to ensure the will of Parliament is upheld shows what extraordinary times we now live in. The House has rejected no deal, businesses and trade unions are united in rejecting no deal and there is no majority for it across the country."
Mr Corbyn added: "In trying to diminish the act, the Government's spin doctors have branded it the Surrender Bill and ministers have dutifully trotted out this phrase in the media."
It came after the prime minister's official spokesman said he "will not be asking for an extension" to Brexit, despite a new law which requires him to seek a further delay if he cannot get a new deal.
The spokesman said ministers did not intend to break the law, but added that "the Prime Minister's Government will not be extending the Article 50 process. We will be leaving on October 31."
Liberal Democrat leader Jo Swinson said it was "absolutely astonishing" to for the Commons to be debating "whether prime minister is going to adhere to the rule of law".
She added: "There's a sense of arrogance, he acts as if the rules don't apply to him and I do not put anything past our Prime Minister on what he might engineer."
SNP Westminster leader Ian Blackford went a step further, saying the "Prime Minister must resign" if he chooses to ignore the new law.
He said: "The Prime Minister says he would rather die in a ditch than write to seek an extension to protect our economy from falling off the cliff edge. "If that is the course that he chooses, then the Prime Minister must resign. Undermining democracy at every turn, the Prime Minister simply cannot be trusted.
"The rule book has been well and truly ripped up. And with it, democracy and decency. Shredded by a cult of Brexit fanboys in Number 10. Unfit to govern, unwilling to govern. What a despicable state of affairs."
Responding to the debate, Foreign Secretary Dominic Raab said: "This Government will always respect the rule of law. That's been our clear position consistently and frankly it's outrageous that that is even in doubt.
"Of course, how the rule of law will be respected is normally straightforward but sometimes it can be more complex because there are conflicting laws or competing legal advice."
Mr Corbyn noted the Prime Minister's absence in the Commons, saying: "He's certainly not here to reply to his debate where I believe he ought to be since the motion is specifically directed towards him."
The night will end with a vote under the Fixed Terms Parliament Act, when Mr Johnson will seek to call an early general election, however opposition MPs are planning to vote down the motion.
They instead agreed that when Parliament returns following prorogation, they will vote down the Queen's Speech and trigger a general election.
A Labour party spokeswoman said: "All leaders agreed that they would not support Boris Johnson's ploy to deny the people their decision by crashing us out of the EU with no deal during a general election campaign."
Former Tory attorney general Dominic Grieve, who applied for the night's first SO24 emergency debate, told MPs that the suspension of Parliament left them with little time to debate.
He said: "The House is about to be prorogued for five weeks, two weeks after we return is the anticipated date on which we are going to leave the European Union.
"There is much which is left undebated and, in particular, we are not going to have an opportunity to ask necessary questions of the Government both in relation to its own prepared documents under Yellowhammer, which it has prepared for its own use in relation to the risks of a no deal."